Electrochemical reduction, radical anions, and dehalogenation of fluorinated/chlorinated 2,1,3-benzothia/selenadiazoles

Leonid A. Shundrin, Irina G. Irtegova, Pavel A. Avrorov, Tatiana F. Mikhailovskaya, Arkady G. Makarov, Alexander Yu Makarov, Andrey V. Zibarev

Research output: Contribution to journalArticlepeer-review

2 Citations (Scopus)


At the first stage of electrochemical reduction in DMF, fluorinated/chlorinated 2,1,3-benzothia/selenadiazoles formed long-lived radical anions characterized by EPR and DFT. Gas-phase electron affinities (EA1) from DFT correlated well with the first-peak potentials separately for S and Se derivatives, and the latter were found to be better electron acceptors than the former in contrast to the atomic EA1 and Allen electronegativity. At the second stage, chalcogen-and halogen-dependent dehalogenation proceeded: non-hydrodefluorination of selenadiazoles through their n-electron activation (n ≥ 2), and hydrodechlorination of thia/selenadiazoles through H+ addition to their dianions. These differ from dehalogenation of related (aza) aromatics (e.g. benzenes, naphthalenes, quinoxalines).

Original languageEnglish
Pages (from-to)166-180
Number of pages15
Issue number3
Publication statusPublished - 25 Jun 2017


  • 2,1,3-benzoselenadiazoles
  • 2,1,3-Benzothiadiazoles
  • Chlorinated
  • Cyclic voltammetry
  • Dehalogenation
  • DFT
  • EPR
  • Fluorinated
  • Radical anions


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